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$2,495,000

3
Beds
3
Baths
4,537
Sqft

33 Pen Key Drive, Upper Matecumbe Key, Florida, 33036

By contacting this agent you agree to these Terms and Conditions.
Home Florida Upper Matecumbe Key
Legacy Retreat in Islamorada - Gated Waterfront Estate with
Legacy Retreat in Islamorada - Gated Waterfront Estate with
Legacy Retreat in Islamorada - Gated Waterfront Estate with
Legacy Retreat in Islamorada - Gated Waterfront Estate with
Legacy Retreat in Islamorada - Gated Waterfront Estate with
MLS# 616008

Legacy Retreat in Islamorada - Gated Waterfront Estate with

$2,495,000

33 Pen Key Drive, Upper Matecumbe Key, Florida, 33036

3
Beds
3
Baths
4,537
Sqft
0.300
Acres
$2,495,000
33 Pen Key Drive, Upper Matecumbe Key, Florida, 33036
3 Beds
3 Baths
4,537 Sqft
0.300 Acres
Legacy Retreat in Islamorada - Gated Waterfront Estate with Marina, Pool & Sunset Point in Exclusive Private Bayfront Club Community. Discover the pinnacle of tropical living in Islamorada, where privacy, elegance, and world-class amenities converge. This expansive Key West-style residence is nestled within one of the Florida Keys' most prestigious gated communities, offering full-time property management, a protected marina, and a lifestyle defined by serenity and sophistication.From the moment you pass through the palm-lined entrance, you're surrounded by manicured tropical beauty. The home's vibrant exterior, wraparound porches, and timeless craftsmanship evoke classic island charm, while interiors are bathed in natural light and framed by lush garden views.Designed for effortless indoor-outdoor living, the spacious three-bedroom layout opens to expansive patios ideal for entertaining or quiet reflection. Towering palms, mature trees, and vibrant bougainvillea create a secluded sanctuary, while the scent of salt air and golden sunsets set the tone for unforgettable evenings.Enjoy exclusive access to a resort-style pool, private beach, kayak launch, the sunset point, and a full-service marina with direct access to world-class sport fishing and boating. Full-time on-site property managers ensure peace of mind, whether you're in your residence or away for the season.Located in the heart of Islamorada, this property offers unmatched proximity to fine dining, boutique shopping, and the legendary waters of the sport fishing capital of the world.Whether you're seeking a seasonal escape or a legacy investment, this home offers the perfect blend of luxury, leisure, and long-term value. Schedule your private tour today and experience the rare combination of privacy, prestige, and paradise.
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Accessibility Features

Accessible Elevator Installed

Property Details

3 Beds
3 Baths
4,537 Sqft
Built 1987
0.300 Acres
No Patio
Garage, Guest, Open
Metal Roof
$10,526 Property Tax
Penn Key Club (83) Community
$8,350 Yearly HOA Fee
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Location

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Contact Information

Eric M. Rizzo
Ocean Sotheby's International Realty
erizzo@oceansir.com
305-394-3062
Please say you found it on BarrierFreeHome.com. Property courtesy of LHUB

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All information provided is deemed reliable but is not guaranteed and should be independently verified.

About Upper Matecumbe Key

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Ad Statistics

Ad Number
6476507
Viewed
1 time
Added
Aug 01, 2025
Updated on
Oct 15, 2025

Listing Information

Data Source
Florida Keys Board of REALTORS®
Source Property ID
616008

Disclaimer

All information provided is deemed reliable but is not guaranteed and should be independently verified.

Compliance

Listing Agent: Eric M. Rizzo, Ocean Sotheby's International Realty, 305-394-3062, 305-712-8888 Listing Site, Listing Status: Active
Copyright © 2025 Florida Keys Board of REALTORS®. All rights reserved. All information provided by the listing agent/broker is deemed reliable but is not guaranteed and should be independently verified.

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